Differentiating your products or services is key to scaling sales and becoming a dominant market player. But how can you achieve this in a crowded software landscape? According to Stephen Steers, a sales expert and author of “Superpower Storytelling,” at the Business of Software Conference, storytelling is a powerful way to make your business stand out, attract people, and turn them into customers.
The “Drop the Brush” Moment
Stephen shared a memorable anecdote from Istanbul: A shoe shiner seemed to accidentally drop his brush near potential customers. When someone, like Stephen, was kind enough to pick it up, the shoe shiner insisted on shining their shoes as a thank you. It initiated a sales pitch. Stephen points out that while this specific tactic might be a bit dishonest, the clever part is how the shoe shiner created a situation that made a potential customer want to engage. He calls this your “drop the brush” moment.
How do you get in front of the right people and start a conversation that helps your business move forward?
The shoe shiner’s trick worked because it played on Stephen’s desire to be a good person, helping him “better tell [his] own story”. This is key: storytelling helps your audience see how your story fits with their own story.
Why Storytelling is a Business Superpower
Stories are much more than just entertainment for businesses, especially in software:
- People Remember Stories Better: Stories actually release chemicals in our brains (like oxytocin, cortisol, and dopamine). This helps us remember information incredibly well – up to 22 times better than just hearing facts or figures.
- Buying is Emotional: People make buying decisions based on emotion first, and then use logic to back it up. Stories are a quick way to create that emotional connection.
- Guides Business Decisions: Having a clear company story helps everyone stay on the same page and make consistent decisions. As Stephen’s mentor says, it helps you ask, “Does this make the boat go faster?”. This sets a clear standard.
- Makes You More Human: In B2B sales, even with technology, it’s still about people solving problems for other people. Storytelling makes your business feel more welcoming and relatable.
- Helps You Stand Out: In a market where many companies offer similar things, stories make your product or business more memorable and different from the competition.
Storytelling can boost the rate at which people buy by 30%.
- Increases Sales: Storytelling can boost the rate at which people buy by 30%. With more sales interactions happening online, engaging content like stories is vital to keep people interested and help them imagine themselves succeeding with your solution.
- Simplifies Complexity: In business, especially B2B, multiple people (potentially 7 or more, even more if they already use competitor software) are involved in buying decisions. Stories make complex information easier for people to understand, remember, and share with others, which can make your sales cycle shorter.
The Simple Storytelling Framework
To implement effective storytelling, Stephen introduces a simple framework built on three key components: Three Audiences, Four Questions, and Three Stories.
The 3 Audiences: You need stories ready for..
- Your Prospects: These are the people you want to sell to. Stories help them see themselves as the ‘hero’ who gets a great outcome from using your product. This is crucial in marketing and sales calls. It’s also important for talking to investors.
- Your Team: This includes everyone who helps your business, like co-founders, employees, and even vendors. Stories help everyone understand the company’s mindset, stick to high standards, build trust, and know if their work is helping the business move forward (making the boat go faster).
- Your Life and the Stage: This is for public speaking, podcasts, or even just answering the question “What do you do?”. Having a story makes you more memorable and interesting.
The 4 Essential Questions: Before telling a story to sell something, ask yourself these..
- What’s at Stake? What could someone win or lose? What’s the problem or scary situation if they do nothing? This helps create a sense of urgency. For example, businesses worry about being left behind by AI.
- What does your prospect want to learn or achieve? What are their goals? Your story should show them how taking a specific action (like using your product) helps them reach that goal. For instance, they might want to learn how to use AI to grow their business.
- What do you want them to feel? Because most buying is emotional (95% happens subconsciously), focus on making your audience feel a certain way. Do you want them to feel scared about missing out (FOMO)? Empowered? Excited about what’s possible? Stories help them connect your solution to their own journey of overcoming challenges. Don’t just talk about product features; talk about the great result your product helps them achieve.
- What do you want them to do next? This is where many people go wrong. If you don’t clearly tell people what step to take after hearing your story, they get confused, and confused people do nothing. You must direct them to the next action, like signing up for a demo or scheduling a call. Telling the story makes this easier because people remember information better (65% retention) and can share it.
The 3 Stories You Already Have: These are stories you can use right away..
- Mission: This isn’t just your company goal; it’s your personal ‘why’. What problem or negative idea do you want to fix in the world? Share the moment you knew you had to solve this. Stephen shared his story about being treated poorly after a layoff as his motivation to help founders improve. It shows you’re driven by something bigger than just selling software. Think about where your well-known traits come from.
- Vision: What does the world look like when you achieve your mission? Who do you help and empower with your solution? A big vision attracts more people who want to see it happen.
- Milestones: Share challenging times you’ve overcome as a founder (like struggling to make payroll but succeeding) or big wins you’ve helped clients achieve. These stories show your resilience, leadership, and capabilities, helping your audience believe they can achieve similar success or overcome challenges with your help. What lessons did you learn from these tough situations? You can use client milestone stories (case studies) to show real results. For instance, a public defender using the software to reduce stress and have more time with their family.
Using Storytelling in Practice
Storytelling is particularly effective in the sales process, especially during calls where you interact directly with potential buyers who have already completed 50-90% of their journey. Use stories when handling common objections like “it’s too expensive,” “will this work for me?”, or “is now the right time?”.
Using a “Kryptonite question” early in a call (“So what made you hop on the phone with us today?”) can provide context and an opportunity to share a story about a similar client you helped. Summarizing the prospect’s needs and following up with a relevant client case study demonstrates understanding and proves your solution can deliver results Ending with a question like “Would similar results work well for your business?” directly addresses the “is this a fit?” objection.
Storytelling isn’t a minor skill; it’s a core way to connect, differentiate your software business, and get results.
By understanding the emotional side of buying, knowing what’s at stake for your audience, and clearly sharing your mission, vision, and past successes, you can create stories that really connect and drive action.
For software CEOs, product learners, and senior leaders, mastering storytelling is key not just for selling products, but for inspiring your team and helping your customers become successful in their own right by using your solution.
(This article draws on Stephen Steers‘ talk “Four Questions to Ask Before You Tell a Story That Sells” at Business of Software Conference.)